895570-29-3

Upstream product

• 99-90-1 para-bromoacetophenone 
• 67-68-5 dimethyl sulfoxide 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 

Downstream Products

• 1020208-77-8 3-(methylthio)-2,5-bis(4-bromophenyl)furan 
• 1020208-86-9 4-bromo-3-(methylthio)-2,5-bis(4-bromophenyl)furan 

Relevant academic research and scientific papers

Visible-Light-Driven Z -Selective Reaction of Methyl Ketones with DMSO: A Mild Synthetic Approach to Methylthio-Substituted 1,4-Enedione Promoted by Selectfluor

Here we disclose a simple, visible-light-driven Z -selective synthesis of methylthio-substituted 1,4-enedione in a single step promoted by Selectfluor. Dimethyl sulfoxide is used as both the 'thio' source and the solvent. Molecular iodine and potassium persulfate are used as catalyst and oxidant, respectively. White light (CFL-30W) is used as the light source. The proposed mechanism involves a Kornblum reaction followed by aldol reaction.

Diastereoselective sp3-C–H Functionalization of Arylmethyl Ketones and Transformation of E- to Z-Products Through Photocatalysis

We have developed an efficient metal-free route for the synthesis of 1,4-enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short time. All the reagents and catalysts are cheap and environmentally benign. In addition, the E-isomer of the products can easily be transformed into the Z-isomer by using eosin Y photocatalyst under the irradiation of white CFL.

C-H functionalization of terminal alkynes towards stereospecific synthesis of (E) or (Z) 2-methylthio-1,4-ene-diones

An efficient metal free self-sorting tandem protocol for stereospecific synthesis of 2-thio-1,4-enediones involving C-C double bond formation via direct coupling of terminal alkynes has been developed. The method was also extended to the first synthesis of β-thio-γ-keto-α,β-unsaturated esters via a cross coupling reaction with ethyl glyoxylate. The reaction relies on a first of its kind use of Bronsted and Lewis acids to switch selectivity for the synthesis of an E or a Z-isomer respectively.

A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives

(Chemical Equation Presented) 2-(Methylthio)-1,4-diaryl-2-butene-1,4-dione (3) are prepared from readily available aryl methyl ketones in the presence of copper(II) oxide, iodine, and dimethyl sulfoxide. The success of the cross-coupling reaction of 4-chloroacetophenone with 2-acetylthiophene confirms a proposed self-sorting tandem reaction mechanism. Both Z- and E-isomers of compound 3 are readily converted into the corresponding 3-methylthio 2,5-diaryl furan 7 in good yield through a domino process involving the reduction of the double bond followed by the Paal-Knorr furan synthesis. Meanwhile, 4-bromo-3-methylthio 2,5-diaryl furan 10 is obtained either by the treatment of furan 7 with molecular bromine or by the treatment of diketone 3 with 30% hydrogen bromide in acetic acid solution in one pot. Removal of the methylthio group is accomplished by the treatment of 7 with Raney Ni in ethanol, which affords the diaryl-substituted furan 11 in excellent isolated yield. Selective reduction of the double bond of compound 3 leads to the formation of the saturated 1,4-diketone 13, which is easily converted to the corresponding 3-methylthio-2,5-diaryl-substituted pyrrole 14 and thiophene 15 via the Paal-Knorr cyclization reaction.

Efficient C-C double-bond formation reaction via a new synthetic strategy: A self-sorting tandem reaction

A novel and efficient carbon-carbon double-bond formation reaction via coupling of aryl or heteroaryl methyl ketones has been developed. A dimethyl sulfoxide-iodine-CuO system was proven to be efficient for this reaction and afforded the expected products in good yields. A new synthetic strategy, a self-sorting tandem reaction, was involved in this type of reaction and was presented for the first time.